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Rudman first started working with the Muppets in a summer internship with the Muppet Workshop in 1981, when he was 18 years old. His friend Richard Hunt helped him get a job as a Muppet performer.[3] The following year, he graduated from Highland Park High School in Chicago. After Hunt's passing in 1992, Rudman assumed the roles of Sully, Sonny Friendly, and the right (horns up) half of the Two-Headed Monster. Outside of Sesame Street, he also took over two of Hunt's Muppet Show characters beginning in 2008: Scooter and Janice.

In addition to his work as a Muppeteer on Sesame Street, Rudman has also provided voice-acting for the show, notably as Baby Bear's animated sidekick Hero Guy, as well as in several animated segments. Many Sesame Street cartoons featuring his voicework also include other Muppet performers, such as Joey Mazzarino.

He was nominated for an Emmy Award in 2004 for "Outstanding Performer in a Children's Series" for his work on Sesame Street as Baby Bear and Cookie Monster. He presented a Daytime Emmy in 2013, appearing at the event with Cookie.